I know that many, many people supplement their incomes with freelancing writing and that a good portion transition into full time freelancing writing. This book is full of great insights (I got to read a pre-launch copy!), and Sarah is sharing even more aspects of life as a freelancer in an interview with us.

Let’s start with the big stuff. You seriously made $59,000 in your first year of freelancing?

I know! It’s still hard to believe sometimes, because my approach was very much “Nose to the grindstone, just bring in the business.” There was very little business planning or strategizing that first year, because I was thrown into it from a layoff and wanted to see if I could do it. I was driven by two things: the desire not to go back to work for someone else and the desire to work as productively as possible. I surpassed my full time income working 3-4 hours per day or 15-20 hours per week (sometimes more, sometimes less) by focusing on being productive, focusing, and setting boundaries.

I also want to give a shoutout for my supportive husband, Josh! He held down a job as a teacher to provide us with health insurance and a minimum income. He didn’t “fund” my freelancing (I quickly out-earned his side of our salary), but he certainly made it possible in that we had a minimum income coming in each month.

When you started, did you think it was even possible to earn that much right at the beginning?

I knew it was possible because I read about others do it. And if anyone can do it, any one else can do it! My favorite motivational quote is from Marcus Aurelius:

Because your own strength is unequal to the task, do not assume that it is beyond the powers of man; but if anything is within the powers and province of man, believe that it is within your own compass also.

Whenever I would start to wonder if I could do it, have doubts, or generally feel stupid, I kept returning to the logic that someone out there was doing this, and if anyone could do it, then I could, too. I just had to keep plugging away and finding new approaches to make it happen.

I also have to share how grateful I am to have deepened my faith around the time I was laid off — without the emotional anchor of my church and the ongoing comfort I found in the Bible, I’d be a useless pile of emotions most days.

What was the worst moment of the first year? Do you feel like that is behind you now, for good?

The worst moment was probably my first three or four sales calls/job calls/inquiries. I was just so awkward and uncomfortable “selling myself” and getting the business that there was lots of dead air and “Ummm….”s going on. I still probably have that go on more often than not, but I’m at least much more comfortable talking about what I can do for someone once we’re on a call.

However, I’ve since learned that that’s an important part of growing up: doing something really uncomfortable because I had to. Freelancing forces you to confront a lot of uncomfortable thoughts, feelings, and habits, and while I still hate some of those parts of the process there’s no denying the growth I’ve experienced since then. I can talk about money with a stranger like nobody’s business, and that was something I shied away from at the beginning!

That was a Debbie Downer question. Now, what was the best moment of the first year?

It was actually just a few days after I got laid off: I had just sorted out the process of getting on my husband’s insurance and looking at the “minimum budget numbers” I would need to achieve to keep freelancing and it felt doable at the time. So it was like 11am on a bright October day and I stepped outside with a book and read for a half hour. It was an absolutely amazing first taste of freedom that still sticks with me (there was no one checking in to see if I was on my lunch break, there was no client work I should have been working on, or immediate bills I was worried about… I was just free).

I don’t always feel that way, but I try to stop once a month and appreciate that the only person driving me to work my butt off is me. It’s a heady place to be!

Do your cats appreciate the extra time you spend at home, compared to when you had an out-of-the-house job? Do you appreciate the extra cat time?

I have never been closer to a cat than I am now. The first few months were confusing for both of us, because apparently I would sit in her chair most of the time and she wasn’t having that. (I think it was her chair because she tried nonstop to get on me and the laptop… ).

We’ve fallen into new and better habits since then — I know where to avoid her nap zone and we break for a game of catch in the late morning and early afternoon. (Cats play catch! Especially with these!)

What do you wish you could tell past-tense Sarah? Either Sarah from the beginning of freelancing, or Sarah from before she committed and started her own company.

Reducing stress is a large part of the reason I continue to freelance — I prefer my 15-hr week to the ones I used to work. Still, money is a huge source of stress. I wish past Sarah had done what I’m doing now: stop EVERYTHING and save up a healthy money buffer. If I had a 10K pad in the bank, this past year would have been the same but much less stressful.

It seems like a weird problem to have when I brought in a regular monthly income, but at the time (while you’re stressing about money) you don’t know that that’s what you’re doing. You just know you’re hustling. Seeking the big picture now, I would relax more and focus on the work. I would also hit recommendations and referrals really hard with those first few clients to start that word of mouth process from the beginning.

When were you last on an airplane, and where did you go? (We like airplanes around here.)

Last summer I went to Cincinnati, OH, to investigate a possible full-time job opportunity. As it turned out, that is not the right city for us and the company didn’t have the right salary range for me. Talk about a wasted weekend! It was still an adventure to get away with my husband, though, and we got some HILARIOUS stories from it. It was also awesome to just pick up and go somewhere without checking in with a boss or worrying about vacation time.

At what point did you believe that you could be “a writer,” a term that is often associated with “starving artist”? Do you feel like your current writing fulfills your creative outlet desires?

My husband and I have talked about this idea a few times, and I think it breaks down into two categories: the business of writing and the art of writing. Less than 10% of my income comes from what I would consider creative writing (blogging, ebooks, etc). The rest is very much writing as a business and a science, learning to write marketing materials and make conversions with words. To me, the art of writing would be making my income from short stories, novels, poetry, or just writing as myself on my blog. That kind of stuff takes a different kind of energy and it’s on the backburner for us right now.

However, I WAS surprised when I took my first job as a copywriter early in 2013 (the one I was eventually laid off from). Writing for a living was a weird feeling, and one I thought wasn’t supposed to be possible. As it turns out, plenty of people do! I should throw in a warning there, though: writing for a living as a business has had a significant impact on my desire to write in my free time (journaling, blogging, or even anything that uses a computer). So, beware. Still, I’d do it again in a heartbeat, and I’m learning to use transcription/recording things whenever possible to limit the amount I type.

One thing I absolutely love about your approach is your focus on creating work-life balance, not feeling like you need to work 60 hours per week. Tell us about how you figured out what the right balance looked like, for you.

(PS: Sarah thoroughly covers finding balance and removing that nagging voice in the back of your head in her book.)

Thank you! This was born out of necessity rather than intention, though. I have an autoimmune disease that makes me 1) cook a lot, and 2) not have as much stamina as people think people should have. Which is to say, an 8 hour day does not look good on me anymore. By far the biggest blessing in freelancing is the ability to be as insanely productive as possible and reap the reward from the value of what I do, not the cost of the time it took to do it.

For example, if someone tried to pay me hourly to write a blog post, it might only cost one hour. But when I charge the value of the thing itself, it’s my business as to how long it takes me. If I’m distracted and tired, it might take two hours. If I’m focused and in the zone it might take 45 minutes. That’s the only reason I’ve been able to condense a full workload into 3-4 hours per day or 15-20 hours per week. If I sold my time by the hour, I would not be able to sustain my business.

Freelancing also calls you to consider the big picture a lot: what am I doing with my time, and why am I doing it? If I just wanted money, I could probably work for someone else. But the more I work, the more I try to build a bigger goal for myself in helping other people be free from what burdens them, too (mostly in the form of career advice).

This also corresponds with some of my journey as a Catholic, too: what am I really supposed to be doing with my time? What did a job distract me from in the past, and what is it distracting me from now? If I’m not very careful, I can fall into the trap of working tons and ignoring my relationships, or working instead of reading about my faith. Even though it’s overwhelming sometimes, I feel incredibly lucky to get to explore these thoughts throughout my day.

What is an example of a mental shift that you had to make in order to go from being an employee to being the boss-lady?

Goodness gracious there have been millions! Down to how I write my emails and what kind of punctuation I use, I find I am far less people-pleasing and self-disparaging, and far more likely to explain why I am valuable and experienced. There are so many boundaries lessons that you need to learn to freelance well, and even now I learn new ones every day. How you talk about yourself and your experience decides how much people –literally– think you’re worth.

I am still learning this lesson now as I consider taking on more work and some full time opportunities that have come my way. There’s a traditional undercurrent in my brain that says a 9-5 is an important thing to have, even though I have successfully brought in this income since 2013 and there’s no signs of stopping. It’s amazing the things that pop up that will cause you to question yourself, so you need to be in tune with the boss lady inside who tells that voice to shut up and get back to work!

It also helps to approach new relationships as a boss-lady partner… NOT an employee… because that will help you have a voice in the conversation and set boundaries for the way you work, how much you are paid, and where the relationship goes. No one can or should have control over your decisions, but often we give it to them out of habit or fear.

You just wrote a book that shows how you pulled off earning $59,000 in your first year of freelancing. To me, this seems like a natural progression from your last book about how to leave a teaching career, called Life After Teaching. What precipitated the writing of this new book, Five Figure Writer?

When I tell people what I do, they are always surprised and interested. It breaks my heart that there are some people who don’t understand how someone can make a full-time income without working 40+ hours a week for someone else…. in much the same way it breaks my heart to hear about a teacher struggling to leave the classroom but feeling like no one will hire them.

Both of those are situations I have lived through and was blessed to come out the other side, and they both have guided me to the core of my life goals: empowering people to take their careers in their own hands and maybe not achieve IMMEDIATE ETERNAL HAPPINESS, but at least be satisfied in their work and feel connected to what they do. That might be my suggestion for world peace, actually.

The result? Gathering all of my experience and hard-earned lessons in one place so that someone can make the most of them. The eBook is a good mix of content that’s on my blog, lessons I’ve learned (and credited) to other freelance leaders, and behind-the-scenes information that I don’t share lightly, but I think it’s important to contribute it to the world so that other people can build on that success. It also helps to supplement my income in a creative way that helps others… and what’s better than that?

Thank you so much for joining us, Sarah!

Best of luck with your book, it is awesome.

If you dabble at all in the world of freelancing, even if it is not as a writer, Sarah has some fantastic lessons for you in her book. Find out how to stay efficient, deal with the emotional roller coaster, land more contracts and more.

About Anne

Anne dreams of financial independence and is working her way towards it, whilst still enjoying life. She has a penchant for gift giving, which got her started with her first blog, Unique Gifter. She also loves money (who doesn't?) and needed an outlet to discuss it. Her likes? Seafood, figure skating, road cycling and skater shoes.

Comments

I am about to transition into the world of freelancing and I admit I’m finding hard to get started, or probably more specifically knowing *where* to start. Your book sounds like it might be a good place.

Hi Diane – Just saw your comment *Sorry!*. I messaged you on Twitter — let me know if you have any questions after you get started reading! There’s really plenty of work to go around, it just takes a little courage and a lot of hustle!

Thank you, Kay! One of the best parts of freelancing is that it has deepened my faith life so much — I’ve never had to rely on God so much, and it’s been scary but also freeing… thank you for mentioning that! It is always heartwarming to meet more people open to faith and spirituality online :-).Sarah Greesonbach recently posted…Get to Know Business Sarah

I love reading inspiration posts like this, thank you both for sharing and doing an interview. Sarah – I really like how you were able to nix the people-pleasing and self-disparage (2 things that drive me nuts at my day job) and how your confidence shines being boss-lady. Congrats!Kristin recently posted…Freelancing Doesn’t Have To Be Lonely

Great question, Will — By sales calls I mean to refer to the first phone call with a prospective client. I have pitched all of my business by email or LinkedIn. The only exception might be referrals in which my client emails a friend and our first interaction is on a phone call… otherwise I have not made any cold calls to connect clients with my services.

This was a fantastic interview Anne, I really enjoyed it. I am still on the side of the fence where freelancing is a dream that seems out of reach because of the golden handcuffs – Sarah seems super motivating!Debtless in Texas recently posted…The Refrigerator Repair Episode

Thank you, Debtless! I may not consider it a blessing that I’ve never had a lucrative-paying job… earning a solid middle-ground income made it easier for me to try something new to see if I could out-earn it. If I had a six-figure salary opportunity, this story might be different (though I am on track for $80K this year :-). You could always use those golden handcuffs to build up a golden savings that can carry you through a few trial months of freelancing!

Right on, Holly! And whenever it seems like the jobs are drying up, it helps to remember this and reach out to others who are doing it successfully, too. A lot of my early-on freelancing “negativity” turned out to be a perspective problem.

I am absolutely fascinated. I’m glad I saw this post because J Money mentioned the book last week, I was intrigued, but did nothing further…

I started freelancing last August, in an attempt to become a stay home mom. But the baby got sick, we are two ear surgeries in, and many hours of sleep lost. I found the hustle was confusing and uncoordinated and felt like I was shooting in the dark. I’m thinking this book would give me more focus and structure (which the engineer in me craves).Kirsten recently posted…Depressed and Suicidal Over Student Loans: A Letter To My Search Traffic

Great to hear, Kristen! Once you take a look through please feel free to email me with any questions! Creating that structure (even when it starts to look and feel like you’re working a desk job, haha) is an important part of the process. Sure, I have a shorter day and I can take longer/more frequent vacations, but every successful freelancer I know sets regular business hours and creates a “business model” much like a corporate job. And adding a child into the mix is no small thing! That takes a whole other level of patience and planning that I commend you for.

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The Bottom

You made it all the way to the bottom! Thanks so much for reading.
Did you know that The Bottom is the name of a town on the island of Saba, in the Caribbean? I went there on a trip once.
The other bottoms I think about are my own bottom, and the bottom of the champagne bottle. Often when I find the bottom of the champagne bottle, my own bottom grows. Funny, that.

Thanks for reading!

- Anne

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